Methanol → (6-Benzyl-pyridin-3-yl)-acetohydroximoyl chloride

HRID 78259ノート

反応式

HRID 78259 の反応式
[CH2:1]([C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][N+:16]([O-:18])=O)=[CH:10][N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO.C[O-].[Li+].C(Cl)[Cl:25]>O1CCCC1.[Ti](Cl)(Cl)(Cl)Cl>[CH2:1]([C:8]1[N:9]=[CH:10][C:11]([CH2:14][C:15]([Cl:25])=[N:16][OH:18])=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

7

反応物 4

HCID 887MethanolHCID 6344DichloromethaneHCID 4177230Lithium methanolateHCID 592551352-Benzyl-5-(2-nitro-ethyl)-pyridine

生成物 1

HCID 72262889(6-Benzyl-pyridin-3-yl)-acetohydroximoyl chloride収率 63%

試薬・触媒・溶媒 2

HCID 24193Titanium Tetrachloride触媒HCID 8028Tetrahydrofuran溶媒

実験手順

To 2-benzyl-5-(2-nitro-ethyl)-pyridine (260 mg, 1.1 mmol) described in Manufacturing Example 210-1-6 and methanol (5 mL) was added lithium methoxide (81 mg, 2.1 mmol), which was concentrated under a reduced pressure. Titanium(IV) tetrachloride (0.38 mL, 3.4 mmol) was added dropwise at −76° C. to a suspension of the residue in methylene chloride (5 mL) and tetrahydrofuran (2.5 mL), which was stirred for 20 minutes at room temperature. This reaction solution was added to ice water and extracted with ethyl acetate. The aqueous layer was extracted with ethyl acetate again (four times). The organic layers were combined, washed with aqueous sodium chloride (one time), dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under a reduced pressure, and tetrahydrofuran was added to the residue. The insolubles thus produced were filtered out. The filtrate was concentrated under a reduced pressure to obtain the title compound (180 mg, 63%).

後処理

  1. concentrationwas concentrated under a reduced pressure
  2. extractionextracted with ethyl acetate
  3. extractionThe aqueous layer was extracted with ethyl acetate again (four times)
  4. washwashed with aqueous sodium chloride (one time)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under a reduced pressure, and tetrahydrofuran
  8. additionwas added to the residue
  9. customThe insolubles thus produced
  10. filtrationwere filtered out
  11. concentrationThe filtrate was concentrated under a reduced pressure

出典と根拠

ORDレコード
ord-87052fc53c1d4db39f67ad4173fa2a90
出典データセット
uspto-grants-2014_09
特許番号
US08841327B2

反応ノート

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